JP2009072610A - 非シアノアクリレートレオロジー改良剤を有する塞栓用組成物の使用 - Google Patents
非シアノアクリレートレオロジー改良剤を有する塞栓用組成物の使用 Download PDFInfo
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- JP2009072610A JP2009072610A JP2008288650A JP2008288650A JP2009072610A JP 2009072610 A JP2009072610 A JP 2009072610A JP 2008288650 A JP2008288650 A JP 2008288650A JP 2008288650 A JP2008288650 A JP 2008288650A JP 2009072610 A JP2009072610 A JP 2009072610A
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- cyanoacrylate
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/36—Materials or treatment for tissue regeneration for embolization or occlusion, e.g. vaso-occlusive compositions or devices
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Abstract
【解決手段】マトリックス形成成分、固体凝集物材料、及び、200,000より大きい平均分子量を有する非シアノアクリレートレオロジー改良剤を含有しており、上記マトリックス形成成分は少なくともアルキルシアノアクリレート単量体、安定剤及び可塑剤を含有し、上記固体凝集物材料は少なくとも放射線不透過剤を含有しており、イオン又は血液を含む環境で接触すると凝固する組成物。
【選択図】なし
Description
困難である。脳又は脳幹に生じる傷害及び成長の治療は、特別な周囲の組織の敏感な性質により特に困難である。
使用された。これらの組成物の有用性は、細胞毒性及び重合によって生成された熱の量によって制限される。シアノアクリレート組成物の構造式において、最近の開発は、血管の疾病を治療する際にそのような組成物の有用性を改善した。例えば、2000年1月18日に発行された米国特許6015541号は、生物学的適合のフリーポリマー、生物学的適合の
溶媒、及び、可溶の放射性同位体中の約0.1〜約25重量%の水を含有している固体の集団の腫瘍の治療のための放射性組成物について記載している。生物学的適合のポリマーはシアノアクリレートのフリーポリマー変異体であり、組成物はイリジウム同位体と結合してn−ブチル−2−シアノアクリレート(NBCA)を含有している。そのような組成物はウサギで固体の集団の腫瘍に効果があることが実証されたが、組成物の粘性及び懸濁液の特性は望ましいとは言い難かった。別の不都合は、延長された懸濁液を調整するために、一定で温和な攪拌を必要として、混合後数秒内にイリジウム同位体が定着することである。
述した組成物と比較して、改善された付着特性を実証した。そのような組成物の処理は、AVMへの処理の直前に2つの別個の材料の成分を混合することを含んでいる。1つの成分
は、純粋なリン酸ヒドロキノン及びp−メトキシフェノールを含有しているシアノアクリレート液体単量体を含有している。もう1つの成分は、純粋な粉末化された金、少量の重合前のシアノアクリレートポリマー及び脂肪酸(エチルミリスチン酸塩)を含有している。改善された付着特性は、重合のために必要とされた時間の間、材料を保持される。少量の重合前のシアノアクリレート単量体の結合は組成物中に記載されているが、非シアノアクリレートレオロジー改良剤又は粘度改良剤は記載されていない。
なくとも1つの抑制剤を含有しており、別の成分は、アルキルシアノアクリレート単量体、アルキルエステル化された脂肪酸及び不透過剤から形成された合成凝集物の構造からなる。組成物は、血液との接触で合成凝集物の構造を形成する。これらの組成物は、前述した組成物に関する改善された特性を実証するが、そのような組成物を処理するためにマイクロカテテール導入装置が使用される不注意な組織付着は問題のままである。非シアノアクリレートレオロジー改良剤が、そのような特性を改善することができるという暗示又は認識はない。
まだ問題がある。改善された組成物は、25cPと2000cPとの間の見かけ上の粘度、改善された結合性、高濃度の放射線不透過剤粉末の改善された懸濁液及び放射線不透過剤の特性を有する。さらに、組成物は、水溶液の環境(例えば、血液)との接触で改善された加水分解の安定性を有する固体の組成物を形成する。
オン性環境との接触で、液体の組成物は、弾性のあるポリマーのマトリックスの調和を有している、凝固された組成物を形成して、粘度を急速に増加させる。
月に記載されている。
ルである。本発明は、さらに多数の営利上利用可能な装置(例えば、カテーテル、カテーテルコイル、カテーテルワイヤー、ステント、カテーテルバルーン)を使用して、いくつかの方法を用いてもよい。組成物の導入を充填することに適切な営利上利用可能な装置の例は、SENTRYTM閉塞バルーンシステム(Target Therapeutics社、アメリカ合衆国 カリフォルニア フリーモント)である。方法は、治療学、化学療法、放射線導入装置及び遺伝
子治療組成物を加えて組合せて使用してもよい(本発明の組成物を有する近接性で適切な位置に導入される)。
、対応するアルキルシアノアクリレートポリマーを形成することができる物理的な特性を有する)のアルキル実体である。特異な形式で使用される「アルキルシアノアクリレート単量体」とは、当業者に理解される1以上の単量体を示すように意図される。
メリーランド メルヴィル)のような営利上利用可能な組成物と同様に、ヨウ素化油、臭素化油、又は、それらの混合物が含まれる 。これらの営利上利用可能な材料は、組成
物を放射線不透過性にし、さらに重合の速度を遅くして、液体の単量体の量を少なくしてもよい。さらに、金、プラチナ、タンタル、チタン、タングステン、硫酸バリウム、その他同種のもの、及びそれらの混合物のような金属は、放射線不透過剤の役割をすることができる特性を有する。
行された米国特許6037366号、2000年8月3日に発行されたPCT国際公開WO 00/44287に記載されている。アルキルシアノアクリレート単量体を調整するための出発材料は、例えば、Aldrich Chemical社、Sigma Chemical社又はFluka Chemical社から営利上利用可能であり、当業者に公知の方法によって調整されることができる。
ルコールは、n−ブチル、イソブチル及び2−ヘキシルアルコールである。約1モル当量のアルキルアルコールは、有機溶剤中に1モルのシアノ酢酸と反応される。触媒量のp−トルエンスルホン酸は添加され、混合物は攪拌され、リフラックスして加熱され、適切なアルキルシアノ酢酸を提供する。
レートを提供する。約1モル当量のホルムアルデヒドは、有機アルコール(例えば、メタノール)のような溶媒に溶解される。
、一般に低分子量の電子アクセプターである。組成物中の遊離基を禁じることができる化合物の例は、限定されず、p−メトキシフェノール、ヒドロキノン、グルヨキシド(glyoxides)及びその他同種のものが含まれる。
酸化防止剤の例は、限定されず、ビタミンA、C及びE(例えば、カロテノイド、アスコル
ビン酸、アルファ−トコフェロール、ベータ−トコフェロール、デルタ−トコフェロール、ガンマ−トコフェロール、酢酸塩、それらのエステル及び同種のもの、或いは、それらの混合物)が含まれる。
レオロジー改良剤は、放射線不透過剤と異なり、塞栓用組成物で流体力学特性及び結合性のある特性を変更する。無機微粒子材料は、典型的に放射線不透過剤及び可塑剤の両方に組み入れられる。無機微粒子材料は、フュームドシリカ、ケイ酸土壌、例えば、ベントナイト、或いは、チキソトロピー、疑似塑性、又は塑性の流動性の特性を有するために塞栓性組成物のレオロジーを変更することができる他の無機微粒子ゲル化材料又は懸濁液材料からなる群から選択される。微粒子材料が塞栓用組成物へチキソトロピーの性質を与えれば、レオロジー改良剤のサイズ及び濃度は、適切な微粒子材料の広範囲から選択される。適切な材料は、例えば、直径で約10ナノメータ(0.1ミクロン)のフュームドシリカ粒子を含有しており、一般的に選択される粒子の性質により、直径で約5ミクロン以下の粒子を含有されてもよい。無機微粒子のレオロジー改良剤を含有する塞栓用組成物は、最初の流体力学の剪断速度の環境から別の流体力学の剪断速度の環境まで変化することで外見上の粘度の変化を示す。求められる効力は、典型的に「貧弱な剪断の挙動」として引用される。例えば、マイクロカテーテルによって流動するとき、塞栓用組成物は、低い外見上の粘度を有し、マイクロカテーテルを出て、もはや流動していないとき、比較的高い外見上の粘度を有している。粘度の変化は、アルキルシアノアクリレート単量体の重合に関係していないが、任意の化学反応がない状態で液体の塞栓用組成物の特性である。
れらのエステル、他の生物学的適合の可塑剤、同様なもの、及び、それらの混合物が含まれる。可塑剤がヨウ素化油であり、可塑剤は組成物の放射線不透過性を増強するために組成物に組み入れられる。
Claims (8)
- 脈管性間隙を組織膨張、組織注入、組織閉塞、又は組織塞栓するための薬剤の調製における、アルキルシアノアクリレート単量体、安定剤、可塑剤、200,000より大きい平均分子量を有する非シアノアクリレートレオロジー改良剤、及び放射線不透過剤を含む固体凝集物材料を含有する塞栓用組成物の使用であって、該組成物が、イオン又は血液を含む環境で接触すると凝固するように設計されている、使用。
- 前記塞栓用組成物は、25mpa・s(25cP)以上2000mpa・s(2000cP)以下の外見上の粘度を有する請求項1記載の使用。
- 前記塞栓用組成物は、100mpa・s(100cP)以上300mpa・s(300cP)以下の外見上の粘度を有する請求項2記載の使用。
- 前記塞栓用組成物は、チキソトロピー、疑似塑性、又は塑性を示す請求項1乃至3の何れかに記載の使用。
- 前記凝固された組成物は、加水分解に安定である請求項1乃至4の何れかに記載の使用。
- 前記脈管性間隙は、動静脈奇形、動脈瘤、痩管、又は、腫瘍である請求項1乃至5の何れかに記載の使用。
- 前記組成物は、投薬により動脈瘤の破裂を安定させるか又は緩和する請求項1乃至6の何れかに記載の使用。
- 前記動脈瘤は、脳動脈瘤である請求項7記載の使用。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070032853A1 (en) * | 2002-03-27 | 2007-02-08 | Hossainy Syed F | 40-O-(2-hydroxy)ethyl-rapamycin coated stent |
EP1390084B1 (en) * | 2001-05-01 | 2011-03-23 | A.V. Topchiev Institute of Petrochemical Synthesis | Two-phase, water-absorbent bioadhesive composition |
US7687053B2 (en) * | 2001-08-20 | 2010-03-30 | Boston Scientific Scimed, Inc. | Embolic compositions with non-cyanoacrylate rheology modifying agents |
US7459142B2 (en) * | 2002-06-06 | 2008-12-02 | Micro Therapeutics, Inc. | High viscosity embolizing compositions comprising prepolymers |
US8425549B2 (en) | 2002-07-23 | 2013-04-23 | Reverse Medical Corporation | Systems and methods for removing obstructive matter from body lumens and treating vascular defects |
US20040224864A1 (en) * | 2003-02-26 | 2004-11-11 | Patterson William R. | Sterilized embolic compositions |
US20050025707A1 (en) * | 2003-02-27 | 2005-02-03 | Patterson William R. | Fumed silica embolic compositions |
US20050158272A1 (en) * | 2004-01-07 | 2005-07-21 | Trivascular, Inc. | Methods, compositions and devices for embolizing body lumens |
US8173176B2 (en) | 2004-03-30 | 2012-05-08 | Boston Scientific Scimed, Inc. | Embolization |
US9675476B2 (en) | 2004-05-25 | 2017-06-13 | Covidien Lp | Vascular stenting for aneurysms |
EP2626038B1 (en) | 2004-05-25 | 2016-09-14 | Covidien LP | Flexible vascular occluding device |
EP2419048A4 (en) | 2004-05-25 | 2014-04-09 | Covidien Lp | VACCINE PLANTATION FOR ANEURYSMA |
US7963287B2 (en) | 2005-04-28 | 2011-06-21 | Boston Scientific Scimed, Inc. | Tissue-treatment methods |
US9463426B2 (en) | 2005-06-24 | 2016-10-11 | Boston Scientific Scimed, Inc. | Methods and systems for coating particles |
US20070078207A1 (en) * | 2005-09-30 | 2007-04-05 | Jonn Jerry Y | Stabilizer cyanoacrylate formulations |
US20070184087A1 (en) * | 2006-02-06 | 2007-08-09 | Bioform Medical, Inc. | Polysaccharide compositions for use in tissue augmentation |
WO2007100556A1 (en) | 2006-02-22 | 2007-09-07 | Ev3 Inc. | Embolic protection systems having radiopaque filter mesh |
CA2652753C (en) * | 2006-05-12 | 2015-12-08 | Cordis Corporation | Balloon expandable bioabsorbable drug eluting stent |
EP2023869B1 (en) * | 2006-05-12 | 2019-09-18 | Cardinal Health Switzerland 515 GmbH | Balloon expandable bioabsorbable drug eluting flexible stent |
KR20100106966A (ko) * | 2007-11-12 | 2010-10-04 | 밸러 메디컬, 인코포레이티드 | 의료용 시아노아크릴레이트의 단일 바이알 제형 |
US7972373B2 (en) * | 2007-12-19 | 2011-07-05 | Advanced Technologies And Regenerative Medicine, Llc | Balloon expandable bioabsorbable stent with a single stress concentration region interconnecting adjacent struts |
EP2387959B1 (en) | 2008-04-21 | 2013-11-13 | Covidien LP | Braid-ball embolic devices and delivery systems |
WO2009140437A1 (en) | 2008-05-13 | 2009-11-19 | Nfocus Neuromedical, Inc. | Braid implant delivery systems |
JP5717100B2 (ja) | 2009-02-20 | 2015-05-13 | コヴィディエン リミテッド パートナーシップ | 静脈不全の治療のための静脈閉鎖に対する装置 |
US10143455B2 (en) | 2011-07-20 | 2018-12-04 | Covidien LLP | Enhanced ultrasound visualization of intravascular devices |
US8409269B2 (en) | 2009-12-21 | 2013-04-02 | Covidien Lp | Procedures for vascular occlusion |
US8998947B2 (en) | 2010-09-10 | 2015-04-07 | Medina Medical, Inc. | Devices and methods for the treatment of vascular defects |
US8974512B2 (en) | 2010-09-10 | 2015-03-10 | Medina Medical, Inc. | Devices and methods for the treatment of vascular defects |
WO2012078678A1 (en) | 2010-12-06 | 2012-06-14 | Tyco Healthcare Group Lp | Vascular remodeling device |
WO2012134990A1 (en) | 2011-03-25 | 2012-10-04 | Tyco Healthcare Group Lp | Vascular remodeling device |
US10196543B2 (en) | 2011-03-31 | 2019-02-05 | Adhezion Biomedical, Llc | Fast bonding hair/eyelash extension adhesive compositions based on medical grade high viscosity cyanoacrylates |
CN103547222B (zh) | 2011-05-11 | 2016-02-10 | 柯惠有限合伙公司 | 脉管重塑装置 |
WO2013049448A1 (en) | 2011-09-29 | 2013-04-04 | Covidien Lp | Vascular remodeling device |
US9072620B2 (en) | 2011-11-04 | 2015-07-07 | Covidien Lp | Protuberant aneurysm bridging device deployment method |
US9011480B2 (en) | 2012-01-20 | 2015-04-21 | Covidien Lp | Aneurysm treatment coils |
US8808620B1 (en) | 2012-02-22 | 2014-08-19 | Sapheon, Inc. | Sterilization process design for a medical adhesive |
US9452070B2 (en) | 2012-10-31 | 2016-09-27 | Covidien Lp | Methods and systems for increasing a density of a region of a vascular device |
EP2919668A2 (en) | 2012-11-13 | 2015-09-23 | Covidien LP | Occlusive devices |
US10736758B2 (en) | 2013-03-15 | 2020-08-11 | Covidien | Occlusive device |
US10076336B2 (en) | 2013-03-15 | 2018-09-18 | Covidien Lp | Delivery and detachment mechanisms for vascular implants |
WO2015073704A1 (en) | 2013-11-13 | 2015-05-21 | Covidien Lp | Galvanically assisted attachment of medical devices to thrombus |
CN105899136A (zh) * | 2014-01-07 | 2016-08-24 | 柯惠有限合伙公司 | 包含非聚结性不透射线的纳米颗粒的氰基丙烯酸酯组合物 |
CN106604751A (zh) * | 2014-04-11 | 2017-04-26 | 柯惠Lp公司 | 带标记的手术器械及其制造方法 |
US9713475B2 (en) | 2014-04-18 | 2017-07-25 | Covidien Lp | Embolic medical devices |
US9814466B2 (en) | 2014-08-08 | 2017-11-14 | Covidien Lp | Electrolytic and mechanical detachment for implant delivery systems |
US10478194B2 (en) | 2015-09-23 | 2019-11-19 | Covidien Lp | Occlusive devices |
US10314593B2 (en) | 2015-09-23 | 2019-06-11 | Covidien Lp | Occlusive devices |
US10893869B2 (en) | 2016-03-24 | 2021-01-19 | Covidien Lp | Thin wall constructions for vascular flow diversion |
US10828037B2 (en) | 2016-06-27 | 2020-11-10 | Covidien Lp | Electrolytic detachment with fluid electrical connection |
US10828039B2 (en) | 2016-06-27 | 2020-11-10 | Covidien Lp | Electrolytic detachment for implantable devices |
US11051822B2 (en) | 2016-06-28 | 2021-07-06 | Covidien Lp | Implant detachment with thermal activation |
US10478195B2 (en) | 2016-08-04 | 2019-11-19 | Covidien Lp | Devices, systems, and methods for the treatment of vascular defects |
US10576099B2 (en) | 2016-10-21 | 2020-03-03 | Covidien Lp | Injectable scaffold for treatment of intracranial aneurysms and related technology |
US10675036B2 (en) | 2017-08-22 | 2020-06-09 | Covidien Lp | Devices, systems, and methods for the treatment of vascular defects |
US11065009B2 (en) | 2018-02-08 | 2021-07-20 | Covidien Lp | Vascular expandable devices |
US11065136B2 (en) | 2018-02-08 | 2021-07-20 | Covidien Lp | Vascular expandable devices |
US10912569B2 (en) | 2018-08-22 | 2021-02-09 | Covidien Lp | Aneurysm treatment coils and associated systems and methods of use |
US10905432B2 (en) | 2018-08-22 | 2021-02-02 | Covidien Lp | Aneurysm treatment coils and associated systems and methods of use |
US11278291B2 (en) | 2018-12-17 | 2022-03-22 | Covidien Lp | Devices, systems, and methods for the treatment of vascular defects |
EP4054440B1 (en) | 2019-11-04 | 2024-06-05 | Covidien LP | Manufacturing method of devices for treatment of intracranial aneurysms |
US11931041B2 (en) | 2020-05-12 | 2024-03-19 | Covidien Lp | Devices, systems, and methods for the treatment of vascular defects |
CN112870428B (zh) * | 2021-01-21 | 2022-05-27 | 北京冠合医疗科技有限公司 | 一种显影清晰的栓塞材料及其制备方法 |
CN115364272B (zh) * | 2022-09-09 | 2023-08-08 | 江西博恩锐尔生物科技有限公司 | 柔软度可调的血管栓塞剂及其制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000044287A1 (en) * | 1999-01-29 | 2000-08-03 | Prohold Medical Technologies, Inc. | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE616638A (ja) | 1961-04-20 | |||
US3896077A (en) * | 1966-10-10 | 1975-07-22 | Fred Leonard | Underwater adhesive |
US3728375A (en) | 1971-05-12 | 1973-04-17 | Eastman Kodak Co | Cyanoacrylate adhesive compositions |
US4406878A (en) * | 1978-08-02 | 1983-09-27 | Eastman Kodak Company | Iodinated contrast agent for radiography |
DE2850918A1 (de) * | 1978-11-24 | 1980-06-04 | Bayer Ag | Roentgenopake dentalwerkstoffe auf basis von organischen kunststoffen in pastoeser form |
IL63876A0 (en) | 1980-10-20 | 1981-12-31 | Population Res Inc | Radiopaque cyanoacrylates |
US4713235A (en) * | 1981-05-26 | 1987-12-15 | Crx Medical, Inc. | Radiopaque cyanoacrylates |
CA1225585A (en) * | 1983-06-30 | 1987-08-18 | Maria T. Litvinova | Composition for embolization of blood vessels |
US5322499A (en) | 1985-09-20 | 1994-06-21 | Liprie Sam F | Continuous sheated low dose radioactive core adapted for cutting into short sealed segments |
GB8729140D0 (en) * | 1987-12-14 | 1988-01-27 | Lingner & Fischer Gmbh | Adhesive |
US5326552A (en) * | 1992-12-17 | 1994-07-05 | Sterling Winthrop Inc. | Formulations for nanoparticulate x-ray blood pool contrast agents using high molecular weight nonionic surfactants |
DK0717617T3 (da) | 1993-09-09 | 2001-02-05 | Schering Ag | Mikropartikler indeholdende aktive bestanddele og gas |
US5795331A (en) | 1994-01-24 | 1998-08-18 | Micro Therapeutics, Inc. | Balloon catheter for occluding aneurysms of branch vessels |
DE69503844T2 (de) | 1994-06-08 | 1999-04-22 | Taoka Chemical Co Ltd | Klebemittelzusammensetzung auf Alphacyanoacrylat Basis |
US5739205A (en) * | 1994-06-08 | 1998-04-14 | Taoka Chemical Company, Limited | α-cyanoacrylate adhesive composition |
JPH08259899A (ja) * | 1995-03-23 | 1996-10-08 | Three Bond Co Ltd | シアノアクリレート系接着剤組成物 |
US5795922A (en) * | 1995-06-06 | 1998-08-18 | Clemson University | Bone cement composistion containing microencapsulated radiopacifier and method of making same |
US5591195A (en) | 1995-10-30 | 1997-01-07 | Taheri; Syde | Apparatus and method for engrafting a blood vessel |
US5882334A (en) | 1995-12-04 | 1999-03-16 | Target Therapeutics, Inc. | Balloon/delivery catheter assembly with adjustable balloon positioning |
US5702361A (en) | 1996-01-31 | 1997-12-30 | Micro Therapeutics, Inc. | Method for embolizing blood vessels |
US5817343A (en) | 1996-05-14 | 1998-10-06 | Alkermes, Inc. | Method for fabricating polymer-based controlled-release devices |
ATE230269T1 (de) * | 1996-05-31 | 2003-01-15 | Micro Therapeutics Inc | Zusammensetzungen zur verwendung bei der embolisierung von blutgefässen |
US5925683A (en) * | 1996-10-17 | 1999-07-20 | Target Therapeutics, Inc. | Liquid embolic agents |
US6020004A (en) | 1997-04-17 | 2000-02-01 | Amgen Inc. | Biodegradable microparticles for the sustained delivery of therapeutic drugs |
US6538026B1 (en) * | 1997-09-11 | 2003-03-25 | Provasis Therapeutics, Inc. | Compositions useful for remodeling body spaces |
US6476070B2 (en) * | 1997-09-11 | 2002-11-05 | Provasis Therapeutics Inc. | Compositions useful for remodeling body spaces |
US6037366A (en) | 1997-09-11 | 2000-03-14 | Prohold Medical Technologies, Inc. | Composition for creating vascular occlusions |
US6015541A (en) | 1997-11-03 | 2000-01-18 | Micro Therapeutics, Inc. | Radioactive embolizing compositions |
US6015424A (en) | 1998-04-28 | 2000-01-18 | Microvention, Inc. | Apparatus and method for vascular embolization |
US6203779B1 (en) * | 1999-03-19 | 2001-03-20 | Charlie Ricci | Methods for treating endoleaks during endovascular repair of abdominal aortic aneurysms |
US7687053B2 (en) * | 2001-08-20 | 2010-03-30 | Boston Scientific Scimed, Inc. | Embolic compositions with non-cyanoacrylate rheology modifying agents |
-
2001
- 2001-08-20 US US09/933,316 patent/US7687053B2/en active Active
-
2002
- 2002-07-09 JP JP2003521688A patent/JP4238131B2/ja not_active Expired - Lifetime
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- 2002-07-09 WO PCT/US2002/021532 patent/WO2003016364A1/en active IP Right Grant
-
2008
- 2008-11-11 JP JP2008288650A patent/JP2009072610A/ja active Pending
-
2010
- 2010-02-17 US US12/707,373 patent/US20100144895A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000044287A1 (en) * | 1999-01-29 | 2000-08-03 | Prohold Medical Technologies, Inc. | Cyanoacrylates comprising inhibitors and an opacifying agent as adhesives |
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WO2003016364A1 (en) | 2003-02-27 |
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JP4238131B2 (ja) | 2009-03-11 |
US7687053B2 (en) | 2010-03-30 |
CA2452505A1 (en) | 2003-02-27 |
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